Vilsmeier–Haack Type Formylation on 6-Aryl-1,4-dithiafulvenes and Syntheses of Novel Extended Tetrathiafulvalene Donors

Abstract

The Vilsmeier–Haack type formylations on various 6-aryl-1,4-dithiafulvenes were examined. The furyl derivatives on treatment with an excess of POCl₃ in DMF at room temperature mainly afforded dialdehydes substituted at the 6-position and the furan ring, while the thienyl derivatives and the phenyl derivatives mainly gave monoformylated derivatives substituted at the 6-position. The obtained mono- and dialdehydes were converted into monoaryl-substituted 2,2′-ethanediylidene-bis(1,3-dithiole) derivatives and heteroaromatic ring-inserted [3]dendralene derivatives with triple 1,3-dithiol-2-ylidenes and their TTF-fused analogues. Electrochemical properties of the new π-electron donors were also investigated by cyclic voltammetry.

Key words

tetrathiafulvalene - redox - cyclic voltammetry - Vilsmeier–Haack reaction - heterocycles

• References

• 1 Present address: Department of General Education of Science, National Institute of Technology, Kurume College, Komorino, Kurume 830-8555, Japan.

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